$48+ Cheap flights from Kentucky to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Kentucky to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Kentucky to Chicago
Keep the following information in mind while searching for Kentucky to Chicago flight deals. Data was last updated June 12, 2025.
Round-trip from | $90 (FlightHub) |
|---|---|
One-way from | $48 (FlightHub) |
Popular in | March |
Cheapest in | April |
Average price | $275 |
Good round-trip deal | $133 or less |
Good one-way deal | $174 or less |
Find flight deals from Kentucky to Chicago
Cheapest flights from Kentucky to ChicagoExplore the most affordable flight options available from Kentucky to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.
Explore the most affordable flight options available from Kentucky to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.
This FlightHub deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This American Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Cheapflightsfares deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This American Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Cheapflights Fare Finder
Customize your flight search to find flights from Kentucky to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
Use the filters below to find and compare flights from Kentucky to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
NashvilleChicago
BNA - ORD
BNAORD
Nashville Intl
Fri 6/27
1:30 pm-3:33 pm
Nonstop2h 03m
Chicago O'Hare Intl
Mon 6/30
4:28 pm-5:57 pm
Nonstop1h 29m
LouisvilleChicago
SDF - ORD
SDFORD
Louisville Intl
Mon 8/4
6:50 pm-7:25 pm
Nonstop1h 35m
Chicago O'Hare Intl
Wed 8/27
3:13 pm-5:38 pm
Nonstop1h 25m
LouisvilleChicago
SDF - MDW
SDFMDW
Louisville Intl
Mon 8/4
3:55 pm-4:10 pm
Nonstop1h 15m
Chicago Midway
Wed 8/27
10:05 am-12:25 pm
Nonstop1h 20m
NashvilleChicago
BNA - MDW
BNAMDW
Nashville Intl
Thu 8/7
8:20 am-10:00 am
Nonstop1h 40m
Chicago Midway
Mon 8/11
7:55 am-9:25 am
Nonstop1h 30m
NashvilleChicago
BNA - ORD
BNAORD
Nashville Intl
Wed 8/20
10:50 am-12:45 pm
Nonstop1h 55m
Chicago O'Hare Intl
Tue 8/26
3:10 pm-4:45 pm
Nonstop1h 35m
LouisvilleChicago
SDF - ORD
SDFORD
Louisville Intl
Mon 9/29
10:55 am-11:33 am
Nonstop1h 38m
Chicago O'Hare Intl
Mon 9/29
7:50 pm-10:30 pm
Nonstop1h 40m
NashvilleChicago
BNA - ORD
BNAORD
Nashville Intl
Thu 10/9
4:20 pm-6:15 pm
Nonstop1h 55m
Chicago O'Hare Intl
Sun 10/12
1:52 pm-3:35 pm
Nonstop1h 43m
LouisvilleChicago
SDF - ORD
SDFORD
Louisville Intl
Tue 9/2
5:30 am-11:50 am
1 stop7h 20m
Chicago O'Hare Intl
Tue 9/9
7:30 am-2:35 pm
1 stop6h 05m
NashvilleChicago
BNA - ORD
BNAORD
Nashville Intl
Sat 10/18
5:53 pm-7:45 pm
Nonstop1h 52m
Chicago O'Hare Intl
Mon 10/20
7:00 am-8:30 am
Nonstop1h 30m
NashvilleChicago
BNA - ORD
BNAORD
Nashville Intl
Thu 7/10
3:07 pm-5:11 pm
Nonstop2h 04m
Chicago O'Hare Intl
Mon 7/14
4:37 pm-6:06 pm
Nonstop1h 29m
Best time to book a flight from Kentucky to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Kentucky with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Kentucky to Chicago
What is the cheapest month to book a flight from Kentucky to Chicago?
Currently, August is the cheapest month in which you can book a flight from Kentucky to Chicago (average of $245). Flying from Kentucky to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from KY to CHI?
Find hourly flight availability from Kentucky to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 12, 2025.
When flying from Kentucky to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Kentucky to Chicago
Explore weekly flight availability from Kentucky to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 12, 2025.
The most flights from USKY to CHI are scheduled on a Wednesday (45 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (31 on average).
Rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.
Temperature in Chicago by month
Plan your trip to Chicago by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated June 12, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and United Airlines from Kentucky to Chicago to help guide your decision. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
Boarding
Entertainment
Overall
Comfort
Crew
Reviews
John,May 2025
PVD - BNA
Food
Boarding
Entertainment
Overall
Comfort
Crew
Reviews
John,May 2025
PVD - BNA
Food
Boarding
Entertainment
Overall
Comfort
Crew
Reviews
John,May 2025
PVD - BNA
Food
Boarding
Entertainment
Overall
Comfort
Crew
Reviews
John,May 2025
PVD - BNA
Food
Boarding
Entertainment
Overall
Comfort
Crew
Reviews
John,May 2025
PVD - BNA
Food
Boarding
Entertainment
Overall
Comfort
Crew
Reviews
John,May 2025
PVD - BNA
Related info for your journey
Find useful and relevant information for your journey from Kentucky to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Kentucky?
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Alternative routes for Kentucky to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top 4 airlines flying from Kentucky to Chicago
Discover the top 4 airlines that operate flights from Kentucky to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$106 | Average$280 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$111 | Average$266 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$113 | Average$142 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$172 | Average$275 | FlexibilityNo cancel fee | On-time63% |